Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations

• DOI: 10.1021/acs.orglett.7b03596
• Publication Date: 2017-12-19T16:45:57Z
• Authors: Wei-Jun Kong; Xingrong Chen; Mingming Wang; Hui-Xiong Dai; Jin-Quan Yu
• Keywords: 01 natural sciences; 3. Good health; 0104 chemical sciences

Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.